Holiday homes by the sea in Islamorada

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B&B and Vacation Rentals
B&B and Vacation Rentals
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FACILITIES

  • Pool
  • Pets Allowed
  • Non Smoking Only

REVIEWS

  • 9+ Exceptional
  • 8+ Fabulous
  • 7+ Very Good

DISTANCE FROM CENTRE

  • Less than 1 km
  • Less than 3 km
  • Less than 5 km

Holiday rental deals in Islamorada

We have selected the best holiday accommodation by the sea in Islamorada. Bluepillow allows you to save money, by finding the best rates on the main vacation rental websites in Islamorada

  • The Caribbean Resort Malayan Palm North

    • Hotel
    With a stay at this apartment in Islamorada (Matecumbe), you'll be within a 15-minute walk of Matecumbe United Methodist Church and Florida Keys Brewing Co.. This apartment is 0.8 mi (1.2 km) from Hurricane ...
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  • Islamorada Condo with ocean access, monthly rentals only

    • 4 Guests · 2Bedrooms
    12.8 Exceptional (15)
    Located on the waterfront, this condo is in Matecumbe, a neighborhood in Islamorada. Bud n' Mary's Dive Center and Florida Keys Brewing Co. are worth checking out if an activity is on the agenda, while ...
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  • Hidden Gem Islamorada | 2nd Floor

    • 4 Guests · 2Bedrooms
    13.3 Exceptional (78)
    Located by the sea, this apartment is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
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  • Hidden Gem Islamorada | 1st Floor

    • 4 Guests · 2Bedrooms
    13.1 Exceptional (90)
    Located on the waterfront, this apartment is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while ...
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  • Islamorada Bungalows Suite 4

    • 2 Guests · 1Bedroom
    13.3 Exceptional (6)
    This apartment is located in Matecumbe, a neighborhood in Islamorada. Bud n' Mary's Dive Center and Florida Keys Brewing Co. are worth checking out if an activity is on the agenda, while those wishing ...
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  • Beacon Reef Condo Oceanfront Islamorada - FREE boat dockage - Water, Elec

    • 4 Guests · 2Bedrooms
    12.3 Exceptional (24)
    Located on the beach, this condo is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
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  • Modern Penthouse with Private Beach & Pool

    • 8 Guests · 4Bedrooms
    10 Exceptional (11)
    Located on the beach, this condo is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
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  • Ultra Luxurious 4 Bedroom ocean front Rental home in Islamorada, Florida Keys

    • 8 Guests · 4Bedrooms
    13.3 Exceptional (6)
    Located near the beach, this condo is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
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  • Ocean & Bay Views. Welcome To Paradise!

    • 2 Guests · 1Bedroom
    10 Exceptional (30)
    Located on the waterfront, this condo is in Matecumbe, a neighborhood in Islamorada. Bud n' Mary's Dive Center and Florida Keys Brewing Co. are worth checking out if an activity is on the agenda, while ...
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  • Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock

    • 6 Guests · 3Bedrooms
    13.3 Exceptional (165)
    Located on the beach, this condo is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
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  • Islamorada Bungalows Suite 3

    • 2 Guests · 1Bedroom
    10.7 Exceptional (6)
    This apartment is located in Matecumbe, a neighborhood in Islamorada. Bud n' Mary's Dive Center and Florida Keys Brewing Co. are worth checking out if an activity is on the agenda, while those wishing ...
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  • 3 bedroom, 3.5 bath luxurious condo 402 at Maison in Islamorada

    • 6 Guests · 3Bedrooms
    This condo is located in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience ...
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  • Islamorada Bungalows Suite 1 Bottom Floor

    • 2 Guests · 1Bedroom
    13.3 Exceptional (6)
    This apartment is located in Matecumbe, a neighborhood in Islamorada. Bud n' Mary's Dive Center and Florida Keys Brewing Co. are worth checking out if an activity is on the agenda, while those wishing ...
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  • Islamorada Bungalows Suite 2 Bottom Floor

    • 2 Guests · 1Bedroom
    13.3 Exceptional (6)
    This apartment is located in Matecumbe, a neighborhood in Islamorada. Bud n' Mary's Dive Center and Florida Keys Brewing Co. are worth checking out if an activity is on the agenda, while those wishing ...
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  • 4 BR Ocean front Condo in Islamorada, FL Keys steps away from pool & sandy beach

    • 8 Guests · 4Bedrooms
    This condo is located in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience ...
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  • The Oasis

    • 8 Guests · 3Bedrooms
    Boasting air-conditioned accommodation with a private pool, sea view and a balcony, The Oasis is set in Islamorada. This beachfront property offers access to a terrace and free private parking. ...
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  • Anglers Reef Paradise

    • 6 Guests · 2Bedrooms
    Anglers Reef Paradise is located in Islamorada, 300 metres from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi. ...
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  • Shades of Palm at The Maison - Special Florida Resident Rates

    • 10 Guests · 4Bedrooms
    Set in Islamorada, 1.1 km from Upper Matecumbe Key and 6.1 km from Windley Key, Shades of Palm at The Maison - Special Florida Resident Rates offers free WiFi and air conditioning. It is situated 22 km ...
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  • Sea Breeze at The Maison - Special Florida Resident Rates

    • 10 Guests · 4Bedrooms
    Set in Islamorada, 2.1 km from Upper Matecumbe Key and 7.1 km from Windley Key, Sea Breeze at The Maison - Special Florida Resident Rates offers free WiFi and air conditioning. It is located 23 km from ...
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  • Casa Blanca @ Islamorada. Beach/heated pool. Kayak/paddle to sandbar. Best restaurants

    • 6 Guests · 2Bedrooms
    Set in Islamorada, close to Windley Key, Casa Blanca @ Islamorada. Beach/heated pool. Kayak/paddle to sandbar. Best restaurants offers accommodation with private beach area, free use of bicycles, water ...
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Bed and breakfast offers in Islamorada by the sea

Are you looking for an accommodation in Islamorada and do you want to save money? Choose from 2 Bed & Breakfasts in Islamorada

  • Anglers Reef Villa 1

    • Hotel
    12.5 Exceptional (9)
    When you stay at Anglers Reef Villa 1 in Islamorada, you'll be on the waterfront, within a 5-minute drive of Windley Key Fossil Reef Geological State Park and Islamorada County Park. This beach villa ...
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  • The Caribbean Resort Royal Palm South

    • Hotel
    10 Exceptional (6)
    Located in Islamorada (Matecumbe), this villa is within a 15-minute walk of Matecumbe United Methodist Church and Florida Keys Brewing Co.. This villa is 0.8 mi (1.2 km) from Hurricane Monument and 1.5 ...
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Farmhouse or Hotel? Choose from the best offers

Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?

  • Farmstays in Islamorada
    Farmstays in Islamorada
  • Hotels in Islamorada
    Hotels in Islamorada

Hotels in Islamorada, our top selection just for you

Are you looking for hotels in Islamorada? Here is a selection of the best hotels in Islamorada

  • Sunset Inn

    • Hotel
    12.2 Exceptional (3148)
    Located in Islamorada, Sunset Inn is within a 5-minute drive of Matecumbe United Methodist Church and History of Diving Museum. This hotel is 0.9 mi (1.4 km) from Hurricane Monument and 0.9 mi (1.5 km) ...
    Check Availability

  • The Caribbean Resort

    • Hotel
    13.1 Exceptional (396)
    A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum. This family-friendly hotel is 2.3 mi (3.7 km) from Bud ...
    Check Availability

  • Breezy Palms Resort

    • Hotel
    11.2 Exceptional (774)
    Facing the beachfront, Breezy Palms Resort offers 3-star accommodation in Islamorada and has an outdoor swimming pool, terrace and private beach area. The property is around 3.1 km from Upper Matecumbe ...
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  • Drop Anchor

    • Hotel
    12 Exceptional (2973)
    With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, a 4-minute walk from Windley Key Fossil Reef Geological State Park and a 3-minute drive from Islamorada County Park. This hotel is ...
    Check Availability

  • Casa Morada

    • Hotel
    12.5 Exceptional (987)
    This privately-owned boutique hotel offers 16 suites and is an adults-only property. Caribbean inspired decor can be found throughout the property. Casa Morada is 600 metres from Upper Matecumbe Key. ...
    Check Availability

  • Islander Resort

    • Hotel
    11.9 Exceptional (3140)
    A tranquil and relaxing retreat directly on the beach in the Florida Keys, this property offers spacious accommodations equipped with microwaves and refrigerators and easy access to attractions and activities. ...
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  • Sands of Islamorada

    • Hotel
    10.8 Exceptional (1219)
    This Islamorada, Florida inn boasts an outdoor pool with a hot tub and a boat dock with a ramp. Guests will be 4 miles from Theater of the Sea and 2 miles of Indian Key Historic State Park. ...
    Check Availability

  • Pelican Cove Resort & Marina

    • Hotel
    10.5 Exceptional (3553)
    Located in Islamorada, Pelican Cove Resort & Marina is by the ocean, within a 5-minute drive of Windley Key Fossil Reef Geological State Park and History of Diving Museum. This beach hotel is 2.7 mi (4.3 ...
    Check Availability

  • Cheeca Lodge & Spa

    • Hotel
    8.7 Fabulous (1600)
    Positioned on 27 acres of lush gardens and 1000 feet of private waterfront, Cheeca Lodge & Spa is a luxury resort in Islamorada, Florida. It features a 9-hole par 3 golf course, on-site spa, and 525-foot ...
    Check Availability

  • The Islands of Islamorada

    • Hotel
    12.8 Exceptional (99)
    Located in Islamorada, 1.7 km from Upper Matecumbe Key, The Islands of Islamorada provides accommodation with an outdoor swimming pool, free private parking, a fitness centre and a bar. ...
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  • Islander Bayside Villas and Boatslips

    • Hotel
    11.5 Exceptional (1137)
    With a stay at Islander Bayside Villas and Boatslips, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 9 minutes by foot from Florida Keys Brewing Co.. This ...
    Check Availability

  • Hadley Resort and Marina

    • Hotel
    10.2 Exceptional (2900)
    This hotel is located in Islamorada, Florida. Hadley Resort and Marina features an outdoor swiming pool and free WiFi throughout the property. ...
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  • La Siesta Resort & Villas

    • Hotel
    11 Exceptional (3419)
    When you stay at La Siesta Resort & Villas in Islamorada, you'll be on the waterfront, within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center. This beach resort is 1 mi ...
    Check Availability

  • Fisher Inn Resort & Marina

    • Hotel
    9.7 Exceptional (3227)
    Located right on the shores of Islamorada, the Fisher Inn Resort & Marina is 14 miles from Key Largo. Guests will enjoy convenient beach access and a boat ramp as well as an outdoor pool and outdoor games ...
    Check Availability

  • Bud N' Mary's Fishing Marina

    • Hotel
    With a stay at Bud N' Mary's Fishing Marina in Islamorada (Matecumbe), you'll be steps from Bud n' Mary's Dive Center and a 2-minute drive from Indian Key Historic State Park. This hotel is 1.6 mi (2.6 ...
    Check Availability

  • Oceanfront Home w/ Patio, Kitchen, & WiFi - Steps to Marina & Activity Center

    • Hotel
    10 Exceptional (2)
    Located by the sea, this resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
    Check Availability

  • Caribbean-Style Family Home w/ Kitchen, WiFi, Outdoor Veranda, & Washer-Dryer

    • Hotel
    10 Exceptional (4)
    Located by the sea, this resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
    Check Availability

  • Large Caribbean-Style Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda

    • Hotel
    10 Exceptional (2)
    Located by the sea, this resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
    Check Availability

  • Spacious Caribbean-Style Home w/ Kitchen, WiFi, & Wraparound Outdoor Veranda

    • Hotel
    10 Exceptional (1)
    Located by the sea, this resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
    Check Availability

  • Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool

    • Hotel
    10 Exceptional (5)
    Located by the sea, this resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
    Check Availability
Discover all the offers >

The best hotels with swimming pool in Islamorada

Book your relaxing holiday, by choosing the best deals at hotels with swimming pools in Islamorada

  • Sunset Inn

    • Hotel
    12.2 Exceptional (3148)
    Located in Islamorada, Sunset Inn is within a 5-minute drive of Matecumbe United Methodist Church and History of Diving Museum. This hotel is 0.9 mi (1.4 km) from Hurricane Monument and 0.9 mi (1.5 km) ...
    Check Availability

  • The Caribbean Resort

    • Hotel
    13.1 Exceptional (396)
    A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum. This family-friendly hotel is 2.3 mi (3.7 km) from Bud ...
    Check Availability

  • Breezy Palms Resort

    • Hotel
    11.2 Exceptional (774)
    Facing the beachfront, Breezy Palms Resort offers 3-star accommodation in Islamorada and has an outdoor swimming pool, terrace and private beach area. The property is around 3.1 km from Upper Matecumbe ...
    Check Availability

  • Drop Anchor

    • Hotel
    12 Exceptional (2973)
    With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, a 4-minute walk from Windley Key Fossil Reef Geological State Park and a 3-minute drive from Islamorada County Park. This hotel is ...
    Check Availability

  • Casa Morada

    • Hotel
    12.5 Exceptional (987)
    This privately-owned boutique hotel offers 16 suites and is an adults-only property. Caribbean inspired decor can be found throughout the property. Casa Morada is 600 metres from Upper Matecumbe Key. ...
    Check Availability

  • Islander Resort

    • Hotel
    11.9 Exceptional (3140)
    A tranquil and relaxing retreat directly on the beach in the Florida Keys, this property offers spacious accommodations equipped with microwaves and refrigerators and easy access to attractions and activities. ...
    Check Availability

  • Sands of Islamorada

    • Hotel
    10.8 Exceptional (1219)
    This Islamorada, Florida inn boasts an outdoor pool with a hot tub and a boat dock with a ramp. Guests will be 4 miles from Theater of the Sea and 2 miles of Indian Key Historic State Park. ...
    Check Availability

  • Pelican Cove Resort & Marina

    • Hotel
    10.5 Exceptional (3553)
    Located in Islamorada, Pelican Cove Resort & Marina is by the ocean, within a 5-minute drive of Windley Key Fossil Reef Geological State Park and History of Diving Museum. This beach hotel is 2.7 mi (4.3 ...
    Check Availability

  • Cheeca Lodge & Spa

    • Hotel
    8.7 Fabulous (1600)
    Positioned on 27 acres of lush gardens and 1000 feet of private waterfront, Cheeca Lodge & Spa is a luxury resort in Islamorada, Florida. It features a 9-hole par 3 golf course, on-site spa, and 525-foot ...
    Check Availability

  • The Islands of Islamorada

    • Hotel
    12.8 Exceptional (99)
    Located in Islamorada, 1.7 km from Upper Matecumbe Key, The Islands of Islamorada provides accommodation with an outdoor swimming pool, free private parking, a fitness centre and a bar. ...
    Check Availability

  • Islander Bayside Villas and Boatslips

    • Hotel
    11.5 Exceptional (1137)
    With a stay at Islander Bayside Villas and Boatslips, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 9 minutes by foot from Florida Keys Brewing Co.. This ...
    Check Availability

  • Hadley Resort and Marina

    • Hotel
    10.2 Exceptional (2900)
    This hotel is located in Islamorada, Florida. Hadley Resort and Marina features an outdoor swiming pool and free WiFi throughout the property. ...
    Check Availability

  • La Siesta Resort & Villas

    • Hotel
    11 Exceptional (3419)
    When you stay at La Siesta Resort & Villas in Islamorada, you'll be on the waterfront, within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center. This beach resort is 1 mi ...
    Check Availability

  • Fisher Inn Resort & Marina

    • Hotel
    9.7 Exceptional (3227)
    Located right on the shores of Islamorada, the Fisher Inn Resort & Marina is 14 miles from Key Largo. Guests will enjoy convenient beach access and a boat ramp as well as an outdoor pool and outdoor games ...
    Check Availability

  • Bud N' Mary's Fishing Marina

    • Hotel
    With a stay at Bud N' Mary's Fishing Marina in Islamorada (Matecumbe), you'll be steps from Bud n' Mary's Dive Center and a 2-minute drive from Indian Key Historic State Park. This hotel is 1.6 mi (2.6 ...
    Check Availability

  • Oceanfront Home w/ Patio, Kitchen, & WiFi - Steps to Marina & Activity Center

    • Hotel
    10 Exceptional (2)
    Located by the sea, this resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
    Check Availability

  • Caribbean-Style Family Home w/ Kitchen, WiFi, Outdoor Veranda, & Washer-Dryer

    • Hotel
    10 Exceptional (4)
    Located by the sea, this resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
    Check Availability

  • Large Caribbean-Style Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda

    • Hotel
    10 Exceptional (2)
    Located by the sea, this resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
    Check Availability

  • Spacious Caribbean-Style Home w/ Kitchen, WiFi, & Wraparound Outdoor Veranda

    • Hotel
    10 Exceptional (1)
    Located by the sea, this resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
    Check Availability

  • Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool

    • Hotel
    10 Exceptional (5)
    Located by the sea, this resort is in Matecumbe, a neighborhood in Islamorada. Florida Keys Brewing Co. and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those ...
    Check Availability
Discover all the offers >

Accommodation and holiday homes in Islamorada

In and around Islamorada the tourist has at disposal several types of holiday accommodation for holidays by the sea, for a lone traveller, a small or large family or even a group.
Islamorada offers: 195 apartments, 33 hotels, 2 b&bs, 199 independent homes, 40 villas and much more by the sea.
The accommodation in this area has positive reviews: the tourists have written 654 reviews with a score of 10.0 Excellent and 63 reviews with a score of 8.0 Very Good, over a total of 23,139 reviews.
For your stay in the charming destination Islamorada, the best features are Pool, Pets Allowed, Non Smoking Only, Kitchen and Spa.

Islamorada: the best offers for the best accommodation and holiday homes

How much doeas it cost to stay in Islamorada? The more economical accommodation in Islamorada has an average cost of 741 pounds per night.

What to do in Islamorada

In Islamorada, the best accommodation near the sea can also be found near the major interest points.

Only a few km from the sea you can find 277 accommodation options available at the best price: 195 Apartments, 2 B&Bs, 33 Hotels, and much more. Below you can find the best apartments near the beaches.
A Islamorada, furthermore, much of the best accommodation is close to the best beaches in the area: 17 Apartments, B&Bs, Hotels, and much more.

The weather forcast in Islamorada

Islamorada: during the year, the average temperature throughout the year is around 26°C. The coldest period of the year is in the month of January where the temperature can drop to 22°C. The hottest month of the year is instead in July where the maximum temperature can reach 29°C.

Top Regions in Islamorada

Windley Key

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